Blown away: Chicago travel diary

I’ve been to a handful of major cities across the U.S. and the world, but for some reason I’ve never felt the urge to go to Chicago. Considering how close it is to Winnipeg (about a 14-hour drive, or a hour and 40 minute flight), it’s never been on my radar of places I really wanted to go to (farther-away places always took priority and I just assumed I would make it down there one day).

Anyways, since my boyfriend had some work stuff going on in the Windy City this past weekend, I figured it was a great a time as any to fly down and make a weekend of it. Since Winnipeg flies direct courtesy of United Airlines, I flew down Friday night and stayed until Sunday evening.

When we got in we grabbed a Lyft downtown to check in at the W Hotel Lakeshore, which is located right next to Lake Michigan with views of the Navy Pier. Since I’m a W Hotels freak, I usually look into staying there first, and thankfully, thanks to a promo on Hotels.com, our stay ended up coming to C$450 for the two nights (which is a total steal for a W Hotel). If you’ve never stayed at a W before, expect uber-trendy accommodations, and wonderful amenities like Bliss body products in the room, a comfy bed, and soft robes.

The Bean in Chicago Roister Chicago The Hampton Social in Chicago Walking down Michigan Avenue, Chicago Downtown Chicago

There are actually two W Hotels in Chicago, the other one located midtown (it was closer to the Willis Tower), however, since it was my first time there, I Googled which one was closest to the Magnificent Mile, and the W Lakeshore won out being about a 10-minute walk from the famous shopping street.

Aside from shopping down Michigan Avenue (which I didn’t do a ton of since the Canadian dollar is still weak – I did buy a shirt at Nordstrom though), we also visited the Bean in Millennium Park (#basic), grabbed a drink in the Signature Room in the John Hancock Building, took some selfies on The Ledge in the Willis tower, ate some amazing food at Michelin star restaurants (Roister and Boka – highly recommend), and just walked around the streets of Chicago.  Oh, and of course we also got late-night Chicago deep dish at Pizzaria Due (we tried Uno’s – the original Chicago deep dish – but it was closed by the time we got there. Pizzaria Due, which is by the same people is kitty corner and open until 1:30 am).

The Ledge at SkyDeck, Willis Tower Chicago Flamingo Wall in Chicago W Hotel Lakeshore Chicago lobby

Although it was a little chillier than expected (thankfully I got a spray tan before the trip, courtesy of Tan on the Run Winnipeg, which had me looking warmer than I felt), I had such an amazing 48 hours in Chicago. With it being so close and convenient, I definitely want to go back and see some of the museums the city has to offer, as well as take part in one of those architecture boat cruises (the lake and rivers were sooo blue – totally not like the water we have here in Winnipeg, which literally translates to “muddy waters”).

Enjoy the photos and let me know your favourite Chicago spots!

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